Here are some real, actual small talk questions I’ve used lately:1. “So, who are you guys using for your taxes this year?”2. “What’s your deductible like with Health Partners? Is there a co-pay?”3. “What sort of productivity tools are you using? What’s your on-boarding process for new clients?”Did you just give yourself a migraine from eye rolls? Are you thinking “Wow, I thought Sarah seemed cool(ish) BUT CLEARLY I WAS MISTAKEN.”Yes? Because those are the very thoughts that I had when I tuned into my own conversations. Between icky gossip, taxes, and real estate, I’ve inadvertently allowed most of my conversations to derail into Snoresville, population me + this person I’m talking to. Conversations – even small talk with strangers – can be an opportunity to connect with our fellow humans, learn new things, or make a new buddy. If we stay away from boring topics or things that bring out our less-than-best-self (mean-spirited gossip or super negative stuff) conversations can be the start of something beautiful. But where does one start? How does one go about having better, more positive, more meaningful conversations? It starts with better questions.

Here are 16 better small talk questions that might just lead to awesome things.

Better small talk questions if you’re trying to be polite, professional, or you don’t know the person super well

“What are you reading/watching/listening to that I need to know about?”Left to my own devices, I’d just watch Broad City repeats and listen to that one Everclear album from 1997 over and over. It’s so enriching and important to read/watch/listen outside of our comfort zones! Asking people this question gives them an opportunity to showcase their excellent taste and act the expert. It also gives you an opportunity to learn about awesome new things!

“What’s awesome in your life right now?”It’s so, so easy for conversations to take a turn towards the negative – why work sucks, how bad the weather’s been, exactly how much we’re dreading tax season. When we start a conversation on a positive note, it will (hopefully) continue in that direction. In a perfectly polite world, your conversation partner will also ask you about what’s awesome in your life and you’ll have an opportunity to voice all the things you’re grateful for. Lovely!

“What cool non-work projects are you working on right now?”Dudes, I’m not going to bore you with my work-related projects and I ask that you return the favor. But I do want to know about how you’re training your bunny for agility competitions, prepping for a long trip, or learning Japanese. It’s inspiring to hear what people are learning, trying, and undertaking – hearing what other people are up to can give us a nudge to start our own New Thing.

“You know a lot about __________, right? What do you think I should do about _________?”People loooooove being asked for advice.* It makes us feel smart, capable, and helpful. So ask your super stylish friend how you should wear this oddly-sized scarf. Ask the amateur brewer what pairs well with Blue Moon. Ask the devoted Dog Mom what you should do with your hyper puppy.

* Not professional advice. Let’s all agree not to ask our accountant friends about deductibles when they’re just trying to find the best slice of cheddar on the cheese tray.

“What are you getting up to this weekend?”Easy, obvious, inoffensive.

“You live in [neighborhood/city], right? Where should I eat/what should I do when I’m over there?”Yet another opportunity to gather useful information for yourself and allow your conversation partner to feel awesome, smart, and useful!

P.S. If you find yourself in South Minneapolis, you should go to Melo Glaze for the peanut butter bombs, Minnehaha Falls for the, um, waterfall, and Book Trader because it is exactly as weird as you think.

“Oh, my gosh. You will not believe what happened to me!”I think that one of the best, easiest ways to break through small talk foolishness is to extend the olive branch. And by ‘olive branch’ I mean ‘share a funny, interesting, personal-ish story about yourself first, to show this person that this is how you conversationally roll.”

Better small talk questions if you’re close friends, bold, or a little weird

Let me be real, friends. If a complete stranger walks up to me at a networking event and opens with “What were you like in high school?” I’m going to turn on my heel and make a bee-line towards the nearest app tray.

But if I’m chatting with an old friend or I’m stuck in an elevator with a stranger and we’ve already worked through the usual questions, I’ll use these deep cuts.

“Tell me something weird about you.”The person you’re talking to can choose exactly how weird they get. Maybe they’ll tell you something tame and sensible or maybe you’ll discover something fascinating or dark. I recently found out that a friend used to be a professional race car driver!

“What’s your superpower?”Yup, it’s another positive question that creates an opportunity for us to say pleasant, happy-fying things! This is a great way to gain insight into someone’s character and it’s fascinating to hear what people view as their greatest strengths. Your Ph.D mathematician friend might think her superpower is organizing closets and your shy, introvert friend might think her superpower is hip hop dance.

For the record, my super powers are a) making a pretty decent dinner out of weird leftovers and pantry staples b) getting strangers to tell me their secrets.

“What’s the coolest/best/funniest/worst/whathaveyou thing that’s happened to you lately?”This is such a great way to turn conversations away from work and real estate! It’s a great way to connect to new people and when you ask them such an open-ended question, you’re giving them space to choose how vulnerable they want to be. Maybe they’ll open up about the horrible meeting they had last week or they might share their go-to hilarious story.

Either way, Boring Conversation Catastrophe averted!

“What were you like in high school?”I LOVE THIS QUESTION, particularly when I’m meeting people in their 30s and 40s and their jock/goth pasts are totally hidden. Sometimes it’s no surprise that She was a cheerleader and He skipped school to hitchhike to Lollapalooza, but I love being surprised by people’s pasts. My sensitive, uber-articulate, Ph.D. husband played hockey for 16 years, had a mullet (!!!), and graduated 168th out of 170 students!

“What was your first job?”It’s long past so there’s nothing to be ashamed of and we can share laughs over fast food uniforms, terrible bosses, and all the things we found while cleaning hotel rooms.

“What are your guilty pleasures?”Now, I don’t really believe in guilty pleasures. I’m not sure a person’s taste in tv shows or music has much to do with their value as a human being. Be that as it may, most of us have the books/tv shows/music we reference in our online dating profiles ….. and the books/tv shows/music we quietly play on repeat.

“What’s your LEAST favorite place?”This is a less-positive question, but the answers are almost always hilarious and unexpected. It’s also a quick peek into someone’s life and mind. One person’s least favorite place is the dentist, another’s is a 17-hour Bolivian bus ride across the altiplano surrounded by drunk silver miners who are peeing into Pringles cans. Also: the seats don’t recline.

“What are you really terrible at?”This was a real dinner party conversation that I encountered a few months ago and I loved it! It was amazing to hear what people were bad at, how they’d learned to work around it or hide it, and all the funny things that had happened because of it. I’m weirdly bad at dates and time zones; I’ve gone to the airport on the wrong day or at the wrong time FIVE TIMES. But I want to hear from you! How do you feel about small talk? What’s your go-to question? And more importantly, what’s your superpower?

Going to remember this list and use it! January every year I’m always asking everyone what there goals are for the year. I also like to ask people about what races they are signing up for, since I hang around a lot of runners.

Another fun thing to ask about is PETS! And then suddenly we’re all crowded around a phone scrolling through pictures of Mr. Whiskers and Friends. Yessss show me all the cute/weirdness! Animal People are the very best people.

“If you could be anywhere right now, where would you be?”
“If you could be doing anything you like right now, what would that be, and why aren’t you doing it?”
“What do love to do the most?”
“What makes you, you?”
“what did you want to grow up to be when you were a kid?”
“what was the most awesome thing you’ve eaten?”

I’m an introvert and LOVE to have fascinating conversations by which I can study people! (not as creepy as it sounds) I’m so thankful for this article because I professionally collect interesting questions! One of my favorites is “What would you do if you were brave enough?” Some people have trouble thinking of an answer so I usually add “Another way to say it is, what are you not doing – because you are afraid of it?”

Yes! I’m a super friendly introvert and could probably ask people questions about themselves for about 4 hours straight. Another good one is “How does it feel to be a [insert job title here]?” It’s a meaningful question that we don’t usually think about!

Thanks for the ideas and examples of how not to wreck small talk. Another game I’ve used and participated in with a mastermind group (where we know one another relatively well professionally but not personally) is Two Truths and a Lie. It’s a lot of fun guessing which is which, and people get a chance to share their own little known facts.

I love this post! I recently asked the (very professional, very polite) new guy at work what he’s currently listening to and he totally floored me by answering that he only really listens to death metal and gangster rap! Then that led to me finding out that he plays four instruments and is learning piano. People are fascinating and they almost never fail to surprise me.

I really love talking about travel. I think “What was your favorite vacation?” or alternatively, “What was the worst thing that ever happened to you on vacation?” can be a good one because it can lead to good stories that reveal a lot but aren’t necessarily intimately personal. People treat things that happened while they were traveling as different from things in their everyday lives, so I think they’re more willing to share.

Excellent! I like to ask about what’s on the house project list or travel wish list or recently read or to read list. It helps steer the convo away from kids and schools (both of which are awesome but….) and also gives people the opportunity to share.

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